(S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate

Base Information

• Chemical Name: (S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate
• CAS No.: 169873-06-7
• Molecular Formula: C₁₆H₁₇NO₆
• Molecular Weight: 319.314
• Mol file: 169873-06-7.mol

Synonyms:

Chemical Property of (S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate

There total 7 articles about (S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

(S)-(+)-tetrahydrofuran-2-yl acetoacetate (169771-75-9) + 2-nitro-benzaldehyde (552-89-6) → (S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate (169873-06-7)

Guidance literature:

With piperidine; acetic acid; 1.) 40 deg C, 30 min, 2.) RT, 15 h;

DOI:10.1021/jm00015a005

Reference yield:

Tetrahydrofurfuryl alcohol (97-99-4) → (S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate (169873-06-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 45 percent / CrO₃, H₂SO₄ / acetone / 20 °C

3: 89 percent / diethyl ether / 1 h / 0 °C

4: 74 percent / NaBH₄ / ethanol / 3 h / Heating

5: 91 percent / xylene / 1 h / 160 °C

6: 68 percent / piperidine, AcOH / 1.) 40 deg C, 30 min, 2.) RT, 15 h

With piperidine; chromium(VI) oxide; sodium tetrahydroborate; sulfuric acid; acetic acid; In diethyl ether; ethanol; acetone; xylene;

DOI:10.1021/jm00015a005

Reference yield:

(S)-tetrahydro-2-furoic acid (87392-07-2) → (S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate (169873-06-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / diethyl ether / 1 h / 0 °C

2: 74 percent / NaBH₄ / ethanol / 3 h / Heating

3: 91 percent / xylene / 1 h / 160 °C

4: 68 percent / piperidine, AcOH / 1.) 40 deg C, 30 min, 2.) RT, 15 h

With piperidine; sodium tetrahydroborate; acetic acid; In diethyl ether; ethanol; xylene;

DOI:10.1021/jm00015a005

upstream raw materials:

2-nitro-benzaldehyde

(S)-(+)-tetrahydrofuran-2-yl acetoacetate

Tetrahydrofurfuryl alcohol

tetrahydro-2-furancarboxylic acid

Downstream raw materials:

(RS)-furnidipine

(SS)-furnidipine

Refernces

• 1、 Alajarin, Ramon,Vaguero, Juan J.,Alvarez-Builla, Julio,Pastor, Manuel,Sunkel, Carlos,et al.. "Synthesis, Structure, and Pharmacological Evaluation of the Stereoisomers of Furnidipine". . p. 2830 - 2841. Retrieved 2007/10/02.